Is Rajon Rondo or Marcus Smart the Bigger Trade Chip for the Boston Celtics?

By drafting Oklahoma State standout Marcus Smart with the No. 6 overall pick in June’s draft, the Boston Celtics served notice anew that theirs is a franchise in the full throes of rebuilding.

Why, after all, would the Celtics put such high stock in a headstrong floor general with solid on-ball instincts, a playmaker’s vision and a far-from-developed jump shot, when they’ve got Rajon Rondo already on the roster?

The wall’s writing couldn’t have been clearer: Eventually, Boston will have to part ways with one of its point guards.

Figuring out which might fetch the bigger return, however, isn’t as cut and dry as it sounds.

Rondo, of course, is the known product: four-time NBA All-Star, two-time NBA All-Defensive First Team, two-time league assist leader and one of the most idiosyncratic—and effective—point guards of his generation.

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At 28 years old, Rondo should, in theory, be in the midst of career prime. Question is, where does he want to spend it?

After missing nearly a full calendar year recovering from a torn ACL, Rondo returned to a team reeling from the loss of Paul Pierce and Kevin Garnett—albeit with a profusion of picks to show for it.

The diminished talent was borne out in Rondo’s production, which saw the point guard register the lowest true-shooting percentage (46 percent) and second-lowest player efficiency rating (15.3) of his career. This despite logging career-par numbers in usage rate (21.3 percent), assists (9.8 per game) and assist rate (47.7 percent).

All while, Boston’s front office has been forced to grapple with something of an existential question: Is Rondo the kind of player you build a contender around or one better suited as an ancillary piece, perhaps elsewhere?

You can understand why the rumors swirl; the Celtics have a difficult decision to make. If Rondo is one of the building blocks of their future, then they must be prepared to pay him big money -- likely more than $100 million over the next five seasons (though maybe they could get a slight discount for tossing in the no-trade clause that would slow the rumor mill in which Rondo has churned throughout his career).

The Celtics, coming off a 57-loss campaign in Brad Stevens' first season at the helm, are in the midst of a rebuilding process with an indeterminate finish line. Boston, having stockpiled assets since last summer when the core of the team was dismantled, is in position to accelerate the process. Alas, there is no definitive roadmap to returning to contender status.

With Rondo slated to become an unrestricted free agent next summer, it certainly behooves Boston to gauge as clearly as possible just how serious he is about seeing the rebuild through. Should the situation sour or the team chemistry become more caustic leading up to the trade deadline, the Celtics will have no choice but to put Rondo on the block in hopes of attracting an asset-rich offer.

Drafting Smart, then, can be seen both as a psychological litmus test and a strategic hedge—a way of preparing for Rondo’s departure without necessarily hastening or orchestrating it.

The risk, then, lies in Boston trading Rondo before it has a full or fair grasp on exactly what kind of player his rookie teammate can be.

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Which is why the Celtics haven’t been shy about using Smart off the ball during the team’s stint at the Orlando Summer League. And while the results have certainly been mixed (Smart connected on just 29 percent from the field, including 26 percent from deep), Celtics director of player personnel Austin Ainge says the gambit is part and parcel with the team’s overall strategy of rotational flexibility:

“Versatility is very important in building a roster,” Ainge told Bleacher Report’s Brian Robb. “We like that Marcus can play the 1 and 2. We like that James [Young] can play the 2 and the 3 and that helps with injuries, rotations, and it’s easier to play guys that can play multiple positions.”

Does head coach Brad Stevens envision a three-guard primary rotation featuring Rondo, Avery Bradley and Smart, with the 20-year-old rookie serving as the third option? Perhaps.

At the same time, when your top three guards are all 6’3” or shorter, you’re inevitably setting yourself up for size mismatches abound—the trio’s capable perimeter defense notwithstanding.

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Coupled with the fact that Bradley is the only one of the three with anything resembling a reliable three-point shot, Boston’s backcourt boasts more than its fair share of holes.

As a pressing question, whether the Celtics can actually build a contender with such an idiosyncratic trio of guards isn’t nearly as important as whether Rondo believes they can. If he doesn’t, Boston simply has to move him (or orchestrate a sign-and-trade), lest the team leaves next summer empty-handed.

Much will depend on exactly how the Celtics choose to approach their rebuild. If, for instance, they still have designs on trading for Kevin Love, whether the All-Star forward prefers to play with Rondo (an established item) or Smart (decidedly not that) stands to figure heavily in the equation.

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As with Rondo and Boston, the Minnesota Timberwolvesaren’t about to let their prize leave for nothing, giving Love more than a little bit of say with respect to who is or isn’t included in any prospective deal. Assuming, of course, the Timberwolves don’t have a better offer on the table.

Equally crucial to the overall equation is whether teams might be willing to trade for Rondo without any assurance he’ll re-sign next summer (again, barring any sign-and-trade scenario).

In short, while Rondo would seem to command more in terms of return assets, the power he wields—wanting to play for a contender, being able to choose his next destination in 2015—means Boston might not be able to demand the kind of return package it wants.

Smart, while certainly riskier, is also a much more fluid asset, cheap and loaded with upside. In other words, he’s the kind of player on which a team already over the rail (like the Timberwolves) might have to roll the dice.

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The balancing act Boston now faces is an intriguing one: showcasing Smart’s talent enough to entice would-be trade partners, without using him so much that the team’s play—and, as a result, Rondo’s interest in sticking around—suffers as a result.

Unless, that is, Stevens somehow figures out how to have his cake and eat it too; use Rondo as a way of attracting more top-flight talent while effectively monitoring whether Smart truly can be the team’s point guard of the future.

As things stand, Boston’s 2014-15 season promises to ring painfully familiar: flashes of future promise amid far fewer wins than losses. The crucial caveats being unforeseen leaps or a timely trade. If it's the latter, you can bet one of its point guards will be included. Just not the one you're probably thinking.

Drafting Smart might seem to spell a certain end to Rondo’s run in Beantown. But in an age where assets are in many ways more valuable than tangible talent, having a piece like Smart could mean the difference between trading into an instant contender and merely hoping it happens.